19 Photos of the Vintage Playboy Clubs

Drinks are on us this International Whiskey Day.

Entertainment & Culture March 27, 2026

Whether you’re a connoisseur or just someone who enjoys a stiff drink, International Whiskey Day is the perfect time to pour yourself a few fingers. Straight up or in a mixed drink, you’ll certainly enjoy your tipple, but wouldn’t it be better if a beautiful Playboy Bunny served it to you? Until our Playboy Clubs closed in 1988, that was a nightly reality for our lucky members.

The first Playboy Club opened in Chicago in 1960, a place where the refined gentlemen who enjoyed the magazine could gather, sipping cocktails and mingling with our iconic, besuited bunnies. The scene was swinging: live performances from soon-to-be stars like Aretha Franklin and Billy Crystal, celebrity clientele, and, of course, the women who made it all happen.

Though the last club closed nearly four decades ago, we’re giving you a taste of what it might have been like to order an old fashioned at the Playboy Club. Sip slowly and enjoy the ride.

Cynthia Maddox, at your service. Photo by Don Bronstein, 1960.
Time to party! Photo by Dwight Hooker
Cocktail time! Photo by Robert Simmons, 1964.
Photo by J. Barry O'Rourke, 1966.
Bunnies in Boston. Photo by Don Zolan
"Tea" time in Boston. Photo by J. Barry O'Rourke
Bunnies in Atlantic City. Photo by Richard Klein, 1981.
Belly up to the bar. Photo by J. Barry O’Rourke.
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